Alloxan (CED0002383)

Record Information
Version1.0
Creation Date2016-05-25 02:34:36 UTC
Update Date2026-08-22 16:05:25 UTC
Accession NumberCHEM020914
Identification
Common NameAlloxan
ClassSmall Molecule
Description
Alloxan is an organic compound with the chemical formula C4H2N2O4 and an average molecular weight of 142.07 g/mol. Alloxan belongs to the pyrimidines and pyrimidine derivatives, a subclass of diazines within the organic compounds. It is further categorized under the superclass of organoheterocyclic compounds. The substance is found in or released from 14 recorded sources across several categories. Within household cleaning and consumer products, it is associated with bleaching agents, perfumes within detergents and soaps, soap detergents, cigar cigarettes, and non electric simulated smoking devices. Its presence in electrical and electronic equipment includes electrodes, hybrid capacitors, sparking plugs, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. Additionally, it is linked to food, food processing and cookware, specifically in the preparation of vinegar, the preparation of wine or sparkling wine, and food preservation.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
2,4,5,6(1H,3H)-PyrimidinetetroneChEBI
2,4,5,6-PyrimidinetetroneChEBI
2,4,5,6-TetraoxohexahydropyrimidineChEBI
5,6-DioxouracilChEBI
5-Oxobarbituric acidChEBI
AlloxaneChEBI
MesoxalylcarbamideChEBI
MesoxalylureaChEBI
NSC 7169ChEBI
PyrimidinetetroneChEBI
5-OxobarbitateGenerator
5-Oxobarbitic acidGenerator
2,4,5,6-PyrimidintetronHMDB
2,4,5,6-PyrimidintetroneHMDB
5-oxo-BarbiturateHMDB
5-oxo-Barbituric acidHMDB
Alloxan 7169HMDB
Alloxan tetrahydratHMDB
Mesoxalyl-ureaHMDB
Chemical FormulaC4H2N2O4
Average Molecular Mass142.070 g/mol
Monoisotopic Mass142.001 g/mol
CAS Registry Number50-71-5
IUPAC Name1,3-diazinane-2,4,5,6-tetrone
Traditional Namealloxan
SMILESO=C1NC(=O)C(=O)C(=O)N1
InChI IdentifierInChI=1S/C4H2N2O4/c7-1-2(8)5-4(10)6-3(1)9/h(H2,5,6,8,9,10)
InChI KeyHIMXGTXNXJYFGB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentPyrimidones
Alternative Parents
Substituents
  • Pyrimidone
  • Hydropyrimidine
  • 2,5-dihydropyrimidine
  • Ketone
  • Carbonic acid derivative
  • Cyclic ketone
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.2 g/LALOGPS
logP-0.85ALOGPS
logP-0.91ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)7.07ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.34 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.77 m³·mol⁻¹ChemAxon
Polarizability10.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9500000000-d176d0d6fcffbf493496Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9400000000-4493e387c163fd19672eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-056r-9000000000-ebb9b8d2b3db01ac1b30Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01ox-9000000000-e390f807cb6126c81a8eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1900000000-5b8617c49e887cf6346cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9400000000-2cc94355c95e93b2971fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ku-9000000000-dd466f209ed4ed32dfc6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-6900000000-4c1a6e3cf8a058b034cfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-ae29c061699f170b84a2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-1d9fa304c38627a77f7dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-4900000000-af3b61eae6a9fbb8e9a4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-90726b17dc36e29c5299Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-90726b17dc36e29c5299Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-3900000000-7554f9bede8cd74601d8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9200000000-2e8e42582aa24cbd48bcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014l-9000000000-87926f5a9b3025440357Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
9009.0Log mg/kg[5100:16000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cruzipain structureClick to view 3D structureCruzipainP25779Trypanosoma cruziPredicted (SEA)616.566
Liver carboxylesterase 1 structureClick to view 3D structureLiver carboxylesterase 1P23141HumansPredicted (SEA)372.197
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)6446.77
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)6393.68
Cyclin-dependent kinase 1 structureClick to view 3D structureCyclin-dependent kinase 1P06493HumansPredicted (SEA)5970.02
Caspase-3 structureClick to view 3D structureCaspase-3P42574HumansPredicted (SEA)2605.07
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)3500.57
Cholinesterase structureClick to view 3D structureCholinesteraseP06276HumansPredicted (SEA)3892.38
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)7156.76
Rho-associated protein kinase 2 structureClick to view 3D structureRho-associated protein kinase 2O75116HumansPredicted (SEA)6882.88
Click to view 3D structureSerine/threonine-protein kinase MRCK alphaQ5VT25HumansPredicted (SEA)6556.23
Interleukin-1 receptor-associated kinase 4 structureClick to view 3D structureInterleukin-1 receptor-associated kinase 4Q9NWZ3HumansPredicted (SEA)6706.24
Serine/threonine-protein kinase pim-2 structureClick to view 3D structureSerine/threonine-protein kinase pim-2Q9P1W9HumansPredicted (SEA)6593.21
Cyclin-dependent kinase 5 structureClick to view 3D structureCyclin-dependent kinase 5Q00535HumansPredicted (SEA)6944.85
SRSF protein kinase 1 structureClick to view 3D structureSRSF protein kinase 1Q96SB4HumansPredicted (SEA)6601.61
Glycogen synthase kinase-3 alpha structureClick to view 3D structureGlycogen synthase kinase-3 alphaP49840HumansPredicted (SEA)6989.54
Rho-associated protein kinase 1 structureClick to view 3D structureRho-associated protein kinase 1Q13464HumansPredicted (SEA)7026.13
Proto-oncogene tyrosine-protein kinase receptor Ret structureClick to view 3D structureProto-oncogene tyrosine-protein kinase receptor RetP07949HumansPredicted (SEA)7013.83
Serine/threonine-protein kinase Chk1 structureClick to view 3D structureSerine/threonine-protein kinase Chk1O14757HumansPredicted (SEA)7079.92
Protein kinase C delta type structureClick to view 3D structureProtein kinase C delta typeQ05655HumansPredicted (SEA)6955.52
Serine/threonine-protein kinase D2 structureClick to view 3D structureSerine/threonine-protein kinase D2Q9BZL6HumansPredicted (SEA)6847.85
Casein kinase I isoform delta structureClick to view 3D structureCasein kinase I isoform deltaP48730HumansPredicted (SEA)6863.81
MAP/microtubule affinity-regulating kinase 3 structureClick to view 3D structureMAP/microtubule affinity-regulating kinase 3P27448HumansPredicted (SEA)6889.42
MAP kinase-activated protein kinase 2 structureClick to view 3D structureMAP kinase-activated protein kinase 2P49137HumansPredicted (SEA)6958.16
Mitogen-activated protein kinase 1 structureClick to view 3D structureMitogen-activated protein kinase 1P28482HumansPredicted (SEA)7129.43
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0002818
FooDB IDFDB023068
Phenol Explorer IDNot Available
KNApSAcK IDC00019778
BiGG IDNot Available
BioCyc IDCPD-3684
METLIN ID252
PDB IDNot Available
Wikipedia LinkAlloxan
Chemspider ID5577
ChEBI ID76451
PubChem Compound ID5781
Kegg Compound IDC07599
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21344938
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23408741
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23473942
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23658878
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23667864
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23762986
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24129090
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24374440
9. Dixon JL, Stoops JD, Parker JL, Laughlin MH, Weisman GA, Sturek M: Dyslipidemia and vascular dysfunction in diabetic pigs fed an atherogenic diet. Arterioscler Thromb Vasc Biol. 1999 Dec;19(12):2981-92.
10. Sakai S, Endo Y, Ozawa N, Sugawara T, Kusaka A, Sayo T, Tagami H, Inoue S: Characteristics of the epidermis and stratum corneum of hairless mice with experimentally induced diabetes mellitus. J Invest Dermatol. 2003 Jan;120(1):79-85.
11. Rayat GR, Rajotte RV, Ao Z, Korbutt GS: Microencapsulation of neonatal porcine islets: protection from human antibody/complement-mediated cytolysis in vitro and long-term reversal of diabetes in nude mice. Transplantation. 2000 Mar 27;69(6):1084-90.
12. Otton R, Carvalho CR, Mendonca JR, Curi R: Low proliferation capacity of lymphocytes from alloxan-diabetic rats: involvement of high glucose and tyrosine phosphorylation of Shc and IRS-1. Life Sci. 2002 Oct 25;71(23):2759-71.
13. Murata M, Imada M, Inoue S, Kawanishi S: Metal-mediated DNA damage induced by diabetogenic alloxan in the presence of NADH. Free Radic Biol Med. 1998 Sep;25(4-5):586-95.
14. Kamilli I, Gresser U: Allopurinol and oxypurinol in human breast milk. Clin Investig. 1993 Feb;71(2):161-4.
15. Murrell GA, Rapeport WG: Clinical pharmacokinetics of allopurinol. Clin Pharmacokinet. 1986 Sep-Oct;11(5):343-53.
16. Mashima R, Nakanishi-Ueda T, Yamamoto Y: Simultaneous determination of methionine sulfoxide and methionine in blood plasma using gas chromatography-mass spectrometry. Anal Biochem. 2003 Feb 1;313(1):28-33.
17. Vaughan LM, Gottehrer A: Effect of xanthine-related compounds on a theophylline assay using theophylline oxidase. Ann Pharmacother. 1992 Dec;26(12):1576-9.
18. Luca VC, Mocanu V: [The history of experimental diabetes in Iasi ]. Rev Med Chir Soc Med Nat Iasi. 2003 Jan-Mar;107(1):227-31.
19. Hande K, Reed E, Chabner B: Allopurinol kinetics. Clin Pharmacol Ther. 1978 May;23(5):598-605.